20 Best Private Drivers In Chicago

Private drivers in Chicago offer practical, no-nonsense transportation solutions for travelers. The best services combine reliable airport transfers with knowledgeable guides who understand the city’s layout and history. My favorite companies employ drivers who share fascinating stories about Chicago’s architecture while navigating between destinations – especially useful during those notorious rush hours.

I particularly like the combination walking-and-driving tours that mix efficient transportation with stops at key landmarks. These smart arrangements help visitors maximize their time, especially at must-see spots like Millennium Park and the Magnificent Mile.

Let’s explore the most dependable private driver services in Chicago.

Key Points

1. Private airport transfer services in Chicago offer reliable, one-way transfers to and from Midway and O’Hare airports with professional, English-speaking drivers.

2. Private custom city tours with knowledgeable guides provide a flexible, personalized experience, allowing visitors to explore top sights, hidden gems, and unique spots in the city.

3. Private walking and architectural tours of Chicago’s iconic buildings and neighborhoods offer a deeper appreciation for the city’s rich history and modern architecture.

4. Private boat tours on the Chicago River showcase the city’s architectural marvels and development, providing a unique perspective from the waterways.

5. Unique cultural experiences, such as skip-the-line art museum tours and creative art-based activities, offer personalized and immersive ways to explore Chicago’s art and heritage.

Chicago Private Custom City Tour With Hotel Pick up

The Chicago Private Custom City Tour with Hotel Pick up offers visitors a personalized exploration of the city’s iconic landmarks and hidden gems.

With a 4.9 rating from 189 reviews, and 98% of travelers recommending it, this private tour provides an exceptional experience at a reasonable price of $539 per group (up to 5 people).

Travelers appreciate the knowledgeable and entertaining guides, who share insights into Chicago’s history, architecture, and culture.

The tour’s flexibility allows visitors to customize their itinerary and explore popular destinations, such as Millennium Park and Wrigley Field, as well as unique spots like the world’s largest Starbucks.

The tour’s accessibility and suitability for various travelers, including those with strollers and infants, make it an ideal choice for both first-time visitors and families.

Read our full review: Chicago Private Custom City Tour With Hotel Pick up Review
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Chicago: One Way Midway Airport Private Transfer

For travelers looking to seamlessly get from their hotel in Chicago to Midway Airport, the Chicago: One Way Midway Airport Private Transfer offers a convenient and comfortable solution.

Priced at $94.00 per group (up to 3 participants), this private transfer service provides a direct, one-hour ride with an English-speaking driver.

Passengers can relax in the private vehicle and avoid the hassle of public transportation or taxi searches. The service includes all fees and taxes, and passengers can enjoy a direct drop-off at the terminal for their flight departure.

However, the service isn’t suitable for wheelchair users.

Read our full review: Chicago: One Way Midway Airport Private Transfer Review
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Best of Chicago: Architecture & Highlights City Private Tour

This compelling Best of Chicago: Architecture & Highlights City Private Tour whisks travelers on an immersive exploration of the city’s iconic landmarks and hidden architectural gems.

Boasting a 4.9-star rating from 95 reviews, the tour is highly recommended by 98% of participants. For just $245 per group, up to 12 guests can experience Chicago’s highlights with a knowledgeable local guide, enjoy snacks, and use a train pass.

The tour covers the city’s rich history and impressive architecture, tailored to the group’s interests. Travelers praise the guide’s enthusiasm and ability to bring the city to life, making this an engaging and informative experience.

Read our full review: Best of Chicago: Architecture & Highlights City Private Tour Review
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Chicago : Loop Private Walking Tour With a Guide

Set out on a captivating private walking tour through Chicago’s iconic Loop district, where the city’s Art Deco and Art Moderne architectural marvels come to life.

This 2-hour guided experience showcases the neighborhood’s most significant buildings, including 30 N La Salle St, 135 S LaSalle St, and 1 N La Salle St.

Led by a knowledgeable local guide, the tour offers insights into Chicago’s architectural evolution and its role in the Art Deco movement.

With optional stops at various sites, the experience can be customized to your interests.

Wheelchair accessible and with a free cancellation policy, this private tour ensures a tailored and flexible exploration of the Loop’s captivating design heritage.

Read our full review: Chicago : Loop Private Walking Tour With a Guide Review
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Skip-the-Line Art Institute of Chicago Semi-Private Tour

Visitors to the Art Institute of Chicago can bypass the lines and enjoy a comprehensive 2.5-hour semi-private tour of the museum’s vast collection.

Capped at 8 participants, this guided tour provides a personalized experience led by knowledgeable guides who enhance guests’ appreciation of the artwork.

With a 5-star rating and 99% traveler recommendation, the tour includes skip-the-line access and all entrance fees.

While guests must meet moderate fitness requirements, the tour is stroller-accessible.

Occasional closures and security restrictions are taken into account, and the experience may vary based on the museum’s current exhibitions.

Read our full review: Skip-the-Line Art Institute of Chicago Semi-Private Tour Review
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Chicago in a Day: Food and Architecture Private Walking Tour

Exploring the vibrant heart of Chicago, this private walking tour offers an immersive experience blending the city’s renowned architecture and mouthwatering local cuisine.

Over 5 hours, you’ll stroll through downtown, admiring iconic landmarks and the picturesque Chicago Riverwalk. Along the way, you’ll sample a full meal’s worth of heritage dishes, from deep-dish pizza to loaded hot dogs, while learning about the city’s diverse culinary history.

With a private, English-speaking guide, this tour is wheelchair accessible and can be booked with no upfront payment and free cancellation.

Whether you’re a first-time visitor or a local, this comprehensive experience promises an unforgettable taste of Chicago’s best.

Read our full review: Chicago in a Day: Food and Architecture Private Walking Tour Review
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Private 45-Minute Chicago Skyline Helicopter Tour

This private 45-minute helicopter tour offers a captivating aerial perspective of Chicago’s iconic skyline. Rated 4.8/5 based on 120 reviews, the tour provides breathtaking views of Millennium Park, Navy Pier, Wrigley Field, and the city’s famous skyscrapers.

Accommodating up to three passengers, the tour is ideal for special occasions and includes noise-cancelling headsets for clear communication with the pilot. Priced at $849 per group, the tour offers exceptional value, with all fees and taxes included, along with free parking, photos, and cancellation up to 24 hours in advance.

With positive reviews highlighting the pilots’ friendliness and professionalism, this helicopter tour is a must-try for those seeking a unique and unforgettable experience.

Read our full review: Private 45-Minute Chicago Skyline Helicopter Tour Review
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Chicago: Customizable Private Sightseeing Tour

For those seeking a more personalized way to experience the Windy City, the Chicago: Customizable Private Sightseeing Tour offers a captivating exploration of the city’s renowned landmarks and hidden gems.

Priced at €297.51 for up to 3 participants, this 2-hour private tour provides the flexibility to customize the itinerary to individual interests.

Highlights include stops at Wrigley Field, Millennium Park, and the Chicago Cultural Center, complemented by drive-bys of iconic sites like the Magnificent Mile and Grant Park.

With complimentary hotel pickup, a knowledgeable local guide, and a private vehicle, this tour promises an immersive and personalized experience of Chicago’s most captivating sights.

Read our full review: Chicago: Customizable Private Sightseeing Tour Review
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Chicago: 45-Minute Private Helicopter Flight for 1-3 People

A private helicopter flight over the iconic skyline of Chicago promises an unparalleled aerial adventure.

Soaring above the city’s most recognizable landmarks, including the Willis Tower and Navy Pier, this 45-minute experience offers breathtaking views.

Priced from $849 for up to 3 people, the flight departs from Schaumburg Regional Airport. Guests will board a private MD500 helicopter with a professional pilot providing live commentary.

Safety is paramount, with sanitized gear and pilots following strict hygiene protocols.

Though not suitable for those over 300 lbs or children under 3, this aerial tour is a must-try for visitors seeking a truly memorable Chicago experience.

Read our full review: Chicago: 45-Minute Private Helicopter Flight for 1-3 People Review
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Chicago: Private Catamaran Sailing for up to 12 People

Guests can sail away on a private catamaran, taking in the breathtaking skyline of Chicago. The 38-foot luxury sailing catamaran accommodates up to 12 people and offers a 2-4 hour experience.

Onboard, guests can enjoy a full kitchen, barbecue grill, Yeti cooler, and Bluetooth radio. The experience can be customized for lessons, tours, or party cruises, and guests can bring their own drinks and food to grill.

A qualified operator is required if guests don’t want to operate the boat themselves, costing an estimated $10-$11 per person per hour plus gratuity.

Certain restrictions apply, so it’s important to review the details before booking this private sailing adventure.

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Chicago: Private Yacht Charter

Chicago’s skyline provides the breathtaking backdrop for private yacht charters that allow visitors to experience the city from a unique vantage point.

These luxurious yachts, ranging from intimate vessels to grand ships, offer unparalleled views of the city’s iconic landmarks, including the Willis Tower and Millennium Park.

Theres some good gourmet catering, relax on the sundeck, or host exclusive events while cruising along the serene waters of Lake Michigan.

Whether it’s a romantic getaway, a corporate function, or a special celebration, a private yacht charter in Chicago promises an unforgettable experience amidst the city’s stunning natural and architectural beauty.

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Chicago: Private Custom Tour With a Local Guide

Visitors to the Windy City can enjoy Chicago’s vibrant culture and iconic landmarks through a private custom tour with a local guide.

These tours offer flexibility, with options ranging from 2 to 8 hours at prices starting from SEK 1,264 per person. Knowledgeable local guides provide English or Spanish-speaking commentary, sharing insider insights and stories that bring the city to life.

Tours are wheelchair accessible, and pickup from accommodation is included. Guests can tailor the itinerary to their interests, with the freedom to explore top sights, hidden gems, and local eateries.

With free cancellation up to 24 hours in advance, these private tours are an excellent way to experience Chicago like a true local.

Read our full review: Chicago: Private Custom Tour With a Local Guide Review
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Chicago River Architecture and History by Private Boat Tour

Gliding down the iconic Chicago River, this private boat tour immerses visitors in the city’s renowned architectural marvels and rich history.

Cruising past towering skyscrapers, guests marvel at the diverse styles that define the Chicago skyline. An expert guide details the fascinating stories behind iconic buildings, from the Gothic splendor of the Tribune Tower to the innovative designs of Marina City.

Travelers gain a deeper appreciation for Chicago’s role in shaping modern architecture as they float beneath movable bridges and along the scenic waterways.

This unique tour offers an unparalleled way to experience the architectural and historical essence of the Windy City.

Read our full review: Chicago River Architecture and History by Private Boat Tour Review
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Shooting + Spinning Private Art Experience

Unleash your inner artist through the captivating Shooting + Spinning Private Art Experience.

This 45-minute activity invites you to use airsoft guns to shoot paint-filled balloons, creating a unique and abstract canvas. With a choice of canvas sizes, from 16×20 inches to 24×24 inches, you’ll have the freedom to express your creativity.

Priced at $92.65 per person, this experience includes seven paint bombs, clothes protection, and the airsoft gun. Rated 5/5 by a satisfied customer, the Shooting + Spinning Private Art Experience promises an unforgettable artistic adventure.

Book now and enjoy the flexibility of reserve now, pay later, and free cancellation.

Read our full review: Shooting + Spinning: Private Art Experience Review
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Chicago O’Hare Airport (ORD): Private Transfer to Chicago

Upon arriving at Chicago O’Hare Airport (ORD), travelers can conveniently book a private transfer to their destination within the city.

The service offers transportation from $186.35 per group of up to 2 people, with a duration of 30 minutes to 1 hour.

Vehicles are air-conditioned, fully licensed, and equipped for all weather conditions.

Drivers speak English, assist with luggage, and wait up to 60 minutes at the airport for arrivals.

The booking process includes instant confirmation, a pre-trip manager contact, and provision of details like luggage quantity and drop-off/pick-up addresses.

This private transfer service provides door-to-door service with no hidden charges, ensuring a seamless travel experience in Chicago.

Read our full review: Chicago O`Hare Airport (ORD): Private Transfer to Chicago Review
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MDW Airport Private Transfer To/From Chicago

For travelers arriving or departing from Midway International Airport (MDW), booking a private transfer to or from downtown/Southside Chicago hotels is a convenient and reliable option.

Priced at $100.85 per group of up to 3 people, the 30-minute transfer allows passengers to travel comfortably in a private vehicle with a professional driver.

With free cancellation up to 24 hours in advance and the ability to reserve now and pay later, the service offers flexibility.

Passengers can avoid the hassle of long taxi lines, busy public transport, and language barriers.

The service includes one-way transfer, professional driver, and porter services, with complimentary waiting time for arrivals and departures.

Read our full review: MDW Airport Private Transfer To/From Chicago Review
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ORD Airport Private Transfer To/From Chicago

Travelers arriving or departing from O’Hare International Airport (ORD) can book a private transfer to or from hotels in Downtown and Southside Chicago.

The 30-minute journey costs from $81.88 per group (up to 3 passengers), with free cancellation up to 24 hours in advance.

Sedan and minivan options are available, all regularly maintained to high-quality standards.

Drivers are professional, and porter services for luggage are provided.

Pickup and drop-off locations are flexible, with free waiting times.

Passengers can avoid the hassle of public transport and enjoy a comfortable, private ride.

This service boasts an overall rating of 4.8/5 based on 5 reviews, making it one of the best private driver options in Chicago.

Read our full review: ORD Airport Private Transfer To/From Chicago Review
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Spinning Private Art Experience

The Spinning Private Art Experience offers a creative and engaging activity for groups of 2 to 10 participants. Lasting 45 minutes, the experience involves an abstract painting technique where paint is dripped, splashed, or poured onto a canvas and then spun to create unique artwork.

Prices start at $76.30 per person, and reservations can be made without an upfront payment. Participants receive a canvas size based on the group size, along with vibrant paints and equipment for applying the paint.

The activity is suitable for families, team building, and private events, allowing for a collaborative creative process. However, the experience has received a 1/5 rating based on a single review indicating a complaint.

Read our full review: Spinning Private Art Experience Review
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Chicago Loop Architecture Private Walking Tour

A three-hour private walking tour of Chicago’s Loop architecture offers visitors an immersive exploration of the city’s rich architectural heritage.

Priced from $227 per person, the tour takes participants to iconic structures like the Marquette Building, Sullivan Center, and Tribune Tower.

Along the way, the knowledgeable local guide provides insights into the birthplace of the modern skyscraper, the influential architects and artistic movements that shaped the city’s skyline, and the historical significance of these architectural gems.

With optional stops for lunch and visits inside select buildings, the tour caters to both architecture novices and enthusiasts, offering a personalized photography experience.

Read our full review: Chicago Loop Architecture Private Walking Tour Review
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From OHare Airport: One-Way Private Transfer to Chicago

After exploring the architectural wonders of Chicago’s Loop on a private walking tour, visitors can seamlessly transition to their next destination with a one-way private transfer from O’Hare International Airport to the heart of the city.

This service costs $78 per group of up to 3 passengers and takes approximately 1 hour. Travelers can enjoy a stress-free ride in an air-conditioned vehicle with a professional driver, who’ll wait for them outside the airport terminal.

With a 4.2/5 overall rating, this transfer option offers convenience and value for money. Passengers can book at least 4 hours prior to arrival and receive driver and meeting point information beforehand, making for a hassle-free experience.

Read our full review: From OHare Airport: One-Way Private Transfer to Chicago Review
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Frequently Asked Questions

Do Private Drivers Offer Child Seats or Booster Seats?

Many private drivers do offer child seats or booster seats upon request. Customers should inquire about these services when booking their ride to ensure the appropriate accommodations are available for transporting children safely.

Can Private Drivers Accommodate Special Requests or Dietary Needs?

Many private drivers can accommodate special requests or dietary needs, such as providing child seats/boosters or accommodating allergies or preferences. They aim to provide a personalized, flexible transportation experience tailored to the passenger’s needs.

What Is the Cancellation Policy for Private Driver Services?

Private driver services typically have a flexible cancellation policy, allowing clients to cancel or reschedule trips with minimal fees, often up to 24 hours in advance. Policies may vary, so it’s best to check with the provider.

Do Private Drivers Provide Water or Other Refreshments During the Ride?

Many private driver services offer complimentary water and other refreshments during the ride to ensure a comfortable and enjoyable experience for passengers. The availability and selection of these amenities can vary between different providers.

Can Private Drivers Assist With Luggage or Heavy Items?

Many private drivers can assist with luggage and heavy items, often offering to help load and unload passengers’ belongings. This additional service can greatly enhance the overall transportation experience.

Sum Up

Chicago’s private drivers offer a range of custom tour options to explore the city’s architecture, art, and highlights. They provide hassle-free airport transfers and personalized experiences, ensuring a seamless and enjoyable visit. Whether you’re seeking a private city tour, an architecture walking tour, or a skip-the-line art museum experience, Chicago’s top private drivers have you covered.